Brother-sister team Miles MacDonnell and Ryan MacDonnell serve as CEO and COO, respectively, of Round Pond Estate—a winery, vineyard and olive mill located on Rutherford land their family has owned since 1983. After years of providing grapes for some of the region’s finest wine producers, the MacDonnell family began making their own wine under the Round Pond label with the inaugural 2002 vintage. Miles and Ryan assumed control of the business in 2003, and today Round Pond Estate produces highly acclaimed Cabernet Sauvignon and Sauvignon Blanc from the family’s 356 acre vineyard. They also craft specialty gourmet foods, including fine red wine vinegars, citrus syrups and olive oil.

“We originally began making wine to become better growers,” Miles says. “We’ve always been passionate about wine, and we wanted to understand fully the intimate connection between what happens in each vineyard micro-block and what happens in the cellar. After our first vintage, we became excited about the winemaking side of things and what we could accomplish with fruit from our family estate.”

Miles MacDonnell, CEO

Miles assumed leadership of Round Pond Estate after a career in auditing with Deloitte. Originally a graduate of Southern Methodist University in psychology and economics, he returned to school in 2005, maintaining his responsibilities at the winery while pursuing his MBA at Boston College. His current role as Round Pond Estate CEO includes heading up viticulture, production, wholesale sales and finance. “Ryan and I are incredibly lucky to live and work with our family on family land,” says Miles. “Basically, we grew up camping out in these vineyards, exploring the river, and riding four-wheelers up and down the valley. As a family, we enjoyed the farm-to-table lifestyle before it was fashionable. The philosophy is a perfect fit for our company, with its estate winery and olive mill.”

Today, Miles lives on the estate with his wife, Katie, and their children, Robbie and Maggie. Ryan lives nearby, and so do their parents. Miles has recently taken up flying again, and on a clear day, you might catch sight of him soaring over the family homes, vineyards, orchards and olive groves in a small aircraft.

Ryan MacDonnell, COO

Ryan MacDonnell, COO, manages direct-to-consumer sales, marketing and the hospitality program at Round Pond Estate. She also heads up the production of olive oil and other specialty gourmet foods. From 2005 to 2007, while Miles pursued his business degree, Ryan oversaw the new winery construction to completion.

“As a family we have always enjoyed the rustic elegance of wine and homegrown food around the table,” says Ryan. “It’s a privilege, now, to be able to share the bounty of our estate with others.”

Ryan spent ten years working outside the winery at Goldman Sachs and the Hewlett Foundation before joining her family at Round Pond Estate in 2003. Her educational background includes a JD from Stanford Law School and an undergraduate degree in Political Economy from UC Berkeley. She lives in a home on the Rutherford estate with her husband, Charles Bracher, and their children Ava, Adeline and Genevieve. They enjoy horseback riding and keep several retired horses on their small ranch.

“Napa Valley has always felt like home,” Ryan says. “As children we spent summers and holidays here, roaming the vineyards. It’s a pleasure to watch my own children and their cousins grow up in this special place together.”